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Compare 375 Vacation Homes in Westport with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (8)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (59)
"Everything was awesome! Would definitely stay here again! "
The price is AED 973
AED 2,027 total
includes taxes & fees
12 May - 13 May
Captain's Cottage - Cold Spring Harbor Water Views

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (20)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home

Business or Weekend escape

9.6 out of 10, Exceptional, (34)
"Very nice owner with great communication. "
The price is AED 275
AED 496 total
includes taxes & fees
8 May - 9 May
Business or Weekend escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Very convenient and plenty of room. Easy to get to NY from Stamford train station and everything we needed nearby."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (31)
"The house was in a great location, was well-stocked and clean, and the host was very responsive. Would definitely stay here again and highly recommend. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (117)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
The price is AED 1,230
AED 2,812 total
includes taxes & fees
20 May - 21 May
New Beach Home near Stamford Downtown/Shippan

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (17)
"Wonderful week at this beautiful home! Great space, comfortable furniture, well equipped. Breathtaking sunrises AND sunsets. Highly recommend this home !"
Ocean Front Beach House with Private Beach Access - Newly Renovated!

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (36)
"Great place magnificent views. It’s a very peaceful place"
Cottage at Sunny Day- Lakeside, views, kayak, dock

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business

Spacious 4-bedroom house with WiFi and AC in awesome Milford

Spacious 4-bedroom house with WiFi and AC in awesome Milford

Charming West Haven Home - Walk to Beach!

8.6 out of 10, Excellent, (11)
"Throughly enjoyed our stay! Was a wonderful experience. The house and area were wonderful!"
Charming West Haven Home - Walk to Beach!

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

10.0 out of 10, Exceptional, (12)
"Clean, cozy and would stay again."
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Sweet Studio w/ Lounge & Pool Table

10.0 out of 10, Exceptional, (1)
"A clean and spacious place to stay in a quiet residential neighborhood. Easy to access. Nice amenities. I didn't get a chance to use the pool table. Thanks for the hospitality."
The price is AED 452
AED 921 total
includes taxes & fees
6 May - 7 May
Sweet Studio w/ Lounge & Pool Table

Stamford Suites

3.0 star property
6.0 out of 10, (29)
"Convenience. Full kitchen and spacious rooms"
The price is AED 735
AED 845 total
includes taxes & fees
18 May - 19 May
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is AED 793
AED 1,114 total
includes taxes & fees
6 May - 7 May
DUNE Fairfield Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.